Roast the honeynut squash: Preheat oven to 425F. Combine squash, 2 Tbsp olive oil, 1 tsp salt, 1 tsp garlic, and 1 tsp cinnamon on a rimmed baking sheet, then toss to combine. Roast for 20 minutes, tossing once halfway through. Set aside until needed.
Roast the chicken breast: Place chicken breast on a rimmed baking sheet, then drizzle with 1 Tbsp olive oil, ½ tsp salt, and ¼ tsp pepper on all sides. Roast until an internal temperature of 165F is reached, about 25-30 minutes. Skin should be crispy. Once cool, remove breast meat from bone, then cut into ½" pieces. Set aside.
Assemble the salad: Divide lettuce evenly between plates. Combine 4 hard boiled eggs, 4 pieces of maple bacon, ⅓ cup candied pecans, ⅓ cup dried cranberries, and ⅓ cup crumbled Syrah cheese in a large mixing bowl. Make the salad dressing.
Make honey Dijon vinaigrette: Combine 1 ½ Tbsp white wine vinegar, 2 tsp dijon mustard, 1 tsp honey, ¼ tsp Kosher salt, pinch of black pepper, and ¼ cup extra virgin olive oil in a small mason jar, then secure with lid. Shake until thoroughly mixed. Add vinaigrette to mixing bowl with salad mix-ins, then toss to combine. Divide dressed toppings between plates, then serve immediately.